Sodium hydride → 4-((Difluoro(6-(4-(trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)methyl)-2-phenyl-5-(trifluoromethyl)oxazole

HRID 406441Notes

Reaction equation

HRID 406441 reaction equation
Cl[C:2]([F:24])([F:23])[C:3]1[N:7]2[CH:8]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=3)[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1.[C:25]1([C:31]2[O:32][C:33]([C:38]([F:41])([F:40])[F:39])=[C:34]([CH2:36][OH:37])[N:35]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[H-].[Na+]>CN(C=O)C>[F:23][C:2]([F:24])([C:3]1[N:7]2[CH:8]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=3)[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1)[O:37][CH2:36][C:34]1[N:35]=[C:31]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[O:32][C:33]=1[C:38]([F:41])([F:40])[F:39]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 581189423-(Chloro-difluoro-methyl)-6-(4-trifluoromethoxy-phenyl)-[1,2,4]triazolo[4,3-a]pyridineHCID 58118959HCID 58118959, compound

Product 1

HCID 581189314-((Difluoro(6-(4-(trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)methyl)-2-phenyl-5-(trifluoromethyl)oxazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 5 mL microwave vial under a nitrogen atmosphere 3-(Chloro-difluoro-methyl)-6-(4-trifluoromethoxy-phenyl)-[1,2,4]triazolo[4,3-a]pyridine (100 mg, 0.275 mmol), (2-phenyl-5-(trifluoromethyl)oxazol-4-yl)methanol (107 mg, 0.440 mmol), and NaH (39 mg, 0.96 mmol) in DMF (3 ml) were combined and stirred for 10 minutes. The reaction mixture was quenched with 1M HCl and concentrated before being purified the product, 4-((difluoro(6-(4-(trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)methyl)-2-phenyl-5-(trifluoromethyl)oxazole, by prep-HPLC(HCl).

Workup

  1. customThe reaction mixture was quenched with 1M HCl
  2. concentrationconcentrated
  3. custombefore being purified the product, 4-((difluoro(6-(4-(trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)methyl)-2-phenyl-5-(trifluoromethyl)oxazole

Sources & evidence

ORD record
ord-e4456b7df11e413a823d4d68dc493e36
Source dataset
uspto-grants-2014_06
Patent number
US08754103B2

Reaction notes

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